[(S)-2-((1R,2R)-1-Benzyloxy-2-hydroxy-1-methyl-oct-3-ynyl)-pyrrolidin-1-yl]-acetonitrile

Base Information

Chemical Name:[(S)-2-((1R,2R)-1-Benzyloxy-2-hydroxy-1-methyl-oct-3-ynyl)-pyrrolidin-1-yl]-acetonitrile
CAS No.:182000-60-8
Molecular Formula:C₂₂H₃₀N₂O₂
Molecular Weight:354.492
Hs Code.:

Synonyms:[(S)-2-((1R,2R)-1-Benzyloxy-2-hydroxy-1-methyl-oct-3-ynyl)-pyrrolidin-1-yl]-acetonitrile

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Chemical Property of [(S)-2-((1R,2R)-1-Benzyloxy-2-hydroxy-1-methyl-oct-3-ynyl)-pyrrolidin-1-yl]-acetonitrile

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Technology Process of [(S)-2-((1R,2R)-1-Benzyloxy-2-hydroxy-1-methyl-oct-3-ynyl)-pyrrolidin-1-yl]-acetonitrile

There total 10 articles about [(S)-2-((1R,2R)-1-Benzyloxy-2-hydroxy-1-methyl-oct-3-ynyl)-pyrrolidin-1-yl]-acetonitrile which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

: 123190-86-3
(1R,7aS)-tetrahydro-1-methyl-1-(hydroxymethyl)-1H,3H-pyrrolo<1,2-c>oxazol-3-one

: 182000-60-8
[(S)-2-((1R,2R)-1-Benzyloxy-2-hydroxy-1-methyl-oct-3-ynyl)-pyrrolidin-1-yl]-acetonitrile

Guidance literature:: Multi-step reaction with 7 steps

1: 100 percent / i-Pr₂NEt / CH₂Cl₂ / 14 h / Ambient temperature

2: aq. KOH / ethanol / 16 h / 80 °C

3: Et₃N / tetrahydrofuran / 2 h / Ambient temperature

4: 91 percent / KH / tetrahydrofuran / 0.5 h / Heating

5: 78 percent / aq. LiBF₄ / acetonitrile / 2 h / 70 °C

6: 77 percent / oxalyl chloride, DMSO / CH₂Cl₂ / 0.5 h / -78 °C

7: 1.) ClTi(O-i-Pr)3 / 1.) THF, -50 deg C

With triisopropoxytitanium(IV) chloride; potassium hydroxide; lithium tetrafluoroborate; oxalyl dichloride; potassium hydride; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; ethanol; dichloromethane; acetonitrile;
DOI:10.1021/ja961640y

Reference yield:

: 123190-88-5
(R)-2-(S)-Pyrrolidin-2-yl-1-(2-trimethylsilanyl-ethoxymethoxy)-propan-2-ol

: 182000-60-8
[(S)-2-((1R,2R)-1-Benzyloxy-2-hydroxy-1-methyl-oct-3-ynyl)-pyrrolidin-1-yl]-acetonitrile

Guidance literature:: Multi-step reaction with 5 steps

1: Et₃N / tetrahydrofuran / 2 h / Ambient temperature

2: 91 percent / KH / tetrahydrofuran / 0.5 h / Heating

3: 78 percent / aq. LiBF₄ / acetonitrile / 2 h / 70 °C

4: 77 percent / oxalyl chloride, DMSO / CH₂Cl₂ / 0.5 h / -78 °C

5: 1.) ClTi(O-i-Pr)3 / 1.) THF, -50 deg C

With triisopropoxytitanium(IV) chloride; lithium tetrafluoroborate; oxalyl dichloride; potassium hydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane; acetonitrile;
DOI:10.1021/ja961640y

Reference yield:

: 51207-70-6
(2S)-N-Benzyloxycarbony-2-(1'-methylethenyl)pyrrolidine

: 182000-60-8
[(S)-2-((1R,2R)-1-Benzyloxy-2-hydroxy-1-methyl-oct-3-ynyl)-pyrrolidin-1-yl]-acetonitrile

Guidance literature:: Multi-step reaction with 10 steps

1: 84 percent / I₂ / acetonitrile

2: AgNO₃ / acetonitrile / 16 h / 80 °C

3: Zn, NH₄OAc / methanol / 0.5 h / 0 °C

4: 100 percent / i-Pr₂NEt / CH₂Cl₂ / 14 h / Ambient temperature

5: aq. KOH / ethanol / 16 h / 80 °C

6: Et₃N / tetrahydrofuran / 2 h / Ambient temperature

7: 91 percent / KH / tetrahydrofuran / 0.5 h / Heating

8: 78 percent / aq. LiBF₄ / acetonitrile / 2 h / 70 °C

9: 77 percent / oxalyl chloride, DMSO / CH₂Cl₂ / 0.5 h / -78 °C

10: 1.) ClTi(O-i-Pr)3 / 1.) THF, -50 deg C

With triisopropoxytitanium(IV) chloride; potassium hydroxide; lithium tetrafluoroborate; oxalyl dichloride; ammonium acetate; iodine; potassium hydride; silver nitrate; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; zinc; In tetrahydrofuran; methanol; ethanol; dichloromethane; acetonitrile;
DOI:10.1021/ja961640y